RU2322449C2 - ПРОИЗВОДНЫЕ АРИЛ 5-ТИО-β-D-ГЛЮКОПИРАНОЗИДА И ТЕРАПЕВТИЧЕСКИЕ СРЕДСТВА ПРИ ДИАБЕТЕ, СОДЕРЖАЩИЕ ИХ - Google Patents

ПРОИЗВОДНЫЕ АРИЛ 5-ТИО-β-D-ГЛЮКОПИРАНОЗИДА И ТЕРАПЕВТИЧЕСКИЕ СРЕДСТВА ПРИ ДИАБЕТЕ, СОДЕРЖАЩИЕ ИХ Download PDF

Info

Publication number: RU2322449C2
Authority: RU; Russia
Prior art keywords: alkyl; thio; group; compound; glucopyranoside
Prior art date: 2002-08-09

Application number

RU2004135914/04A

Other languages

English (en)

Russian (ru)

Other versions

RU2004135914A (ru

Inventor

Масаказу САТО (JP)

Масаказу САТО

Хироюки КАКИНУМА (JP)

Хироюки КАКИНУМА

Хадзиме АСАНУМА (JP)

Хадзиме АСАНУМА

Original Assignee

Тайсо Фармасьютикал Ко., Лтд.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-08-09

Filing date

2003-08-08

Publication date

2008-04-20

2003-08-08 Application filed by Тайсо Фармасьютикал Ко., Лтд. filed Critical Тайсо Фармасьютикал Ко., Лтд.

2005-05-10 Publication of RU2004135914A publication Critical patent/RU2004135914A/ru

2008-04-20 Application granted granted Critical

2008-04-20 Publication of RU2322449C2 publication Critical patent/RU2322449C2/ru

Links

206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 34
239000003814 drug Substances 0.000 title claims abstract description 24
229940124597 therapeutic agent Drugs 0.000 title claims abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 139
125000000217 alkyl group Chemical group 0.000 claims abstract description 113
125000005843 halogen group Chemical group 0.000 claims abstract description 88
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 66
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 65
125000002252 acyl group Chemical group 0.000 claims abstract description 45
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 43
150000003839 salts Chemical class 0.000 claims abstract description 42
125000003277 amino group Chemical group 0.000 claims abstract description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 20
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
230000002401 inhibitory effect Effects 0.000 claims abstract description 10
201000010099 disease Diseases 0.000 claims abstract description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 5
125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
125000000335 thiazolyl group Chemical group 0.000 claims abstract description 5
230000000069 prophylactic effect Effects 0.000 claims abstract description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
239000008194 pharmaceutical composition Substances 0.000 claims abstract 6
108091006269 SLC5A2 Proteins 0.000 claims abstract 2
102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 claims abstract 2
125000003545 alkoxy group Chemical group 0.000 claims description 73
-1 phenoxy, pyrazolyl group Chemical group 0.000 claims description 56
238000002360 preparation method Methods 0.000 claims description 47
125000001424 substituent group Chemical group 0.000 claims description 34
239000003112 inhibitor Substances 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 26
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
229920006395 saturated elastomer Polymers 0.000 claims description 24
125000004423 acyloxy group Chemical group 0.000 claims description 19
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000001589 carboacyl group Chemical group 0.000 claims description 14
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 11
125000004442 acylamino group Chemical group 0.000 claims description 11
125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
229940125396 insulin Drugs 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
229940079593 drug Drugs 0.000 claims description 9
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
229940123208 Biguanide Drugs 0.000 claims description 7
102000004877 Insulin Human genes 0.000 claims description 7
108090001061 Insulin Proteins 0.000 claims description 7
102000023984 PPAR alpha Human genes 0.000 claims description 7
239000003316 glycosidase inhibitor Substances 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims description 7
230000003914 insulin secretion Effects 0.000 claims description 6
102000000853 LDL receptors Human genes 0.000 claims description 5
108010001831 LDL receptors Proteins 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
239000005516 coenzyme A Substances 0.000 claims description 5
229940093530 coenzyme a Drugs 0.000 claims description 5
229940125753 fibrate Drugs 0.000 claims description 5
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
230000003228 microsomal effect Effects 0.000 claims description 5
239000004059 squalene synthase inhibitor Substances 0.000 claims description 5
229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 claims description 4
229940122355 Insulin sensitizer Drugs 0.000 claims description 4
229940124754 PPAR-alpha/gamma agonist Drugs 0.000 claims description 4
102000001494 Sterol O-Acyltransferase Human genes 0.000 claims description 4
108010054082 Sterol O-acyltransferase Proteins 0.000 claims description 4
RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 claims description 4
KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 claims description 4
239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 claims description 4
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 3
229940122069 Glycosidase inhibitor Drugs 0.000 claims description 3
229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 claims description 3
229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
239000002269 analeptic agent Substances 0.000 claims description 2
239000000841 delta opiate receptor agonist Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims 1
150000003626 triacylglycerols Chemical class 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 12
230000000694 effects Effects 0.000 abstract description 9
230000015572 biosynthetic process Effects 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
230000007721 medicinal effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
239000011734 sodium Substances 0.000 description 128
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 44
239000011541 reaction mixture Substances 0.000 description 41
238000005481 NMR spectroscopy Methods 0.000 description 38
238000010898 silica gel chromatography Methods 0.000 description 38
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 36
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
239000002904 solvent Substances 0.000 description 26
239000000843 powder Substances 0.000 description 25
238000005160 1H NMR spectroscopy Methods 0.000 description 24
238000003756 stirring Methods 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
238000000034 method Methods 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
239000007864 aqueous solution Substances 0.000 description 16
125000003710 aryl alkyl group Chemical group 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
239000011780 sodium chloride Substances 0.000 description 15
OSZSMFQZURNRHS-RQICVUQASA-N [(2r,3s,4s,5r)-3,4,5-triacetyloxy-6-hydroxythian-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1SC(O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O OSZSMFQZURNRHS-RQICVUQASA-N 0.000 description 14
239000012074 organic phase Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
125000003118 aryl group Chemical group 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
239000000556 agonist Substances 0.000 description 9
238000001914 filtration Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
229960001031 glucose Drugs 0.000 description 8
239000000825 pharmaceutical preparation Substances 0.000 description 8
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 8
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
125000001691 aryl alkyl amino group Chemical group 0.000 description 7
125000002102 aryl alkyloxo group Chemical group 0.000 description 7
125000004104 aryloxy group Chemical group 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 7
239000008103 glucose Substances 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000000651 prodrug Substances 0.000 description 7
229940002612 prodrug Drugs 0.000 description 7
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
KNWYARBAEIMVMZ-UHFFFAOYSA-N 6-(hydroxymethyl)thiane-2,3,4,5-tetrol Chemical compound OCC1SC(O)C(O)C(O)C1O KNWYARBAEIMVMZ-UHFFFAOYSA-N 0.000 description 5
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
229940125904 compound 1 Drugs 0.000 description 5
239000010949 copper Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
230000001419 dependent effect Effects 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
235000000346 sugar Nutrition 0.000 description 5
239000000725 suspension Substances 0.000 description 5
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 4
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 4
PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 4
HWRPGXGZOLYUAL-UHFFFAOYSA-N 2,4-dibromo-6-[(4-ethylphenyl)methyl]phenol Chemical compound C1=CC(CC)=CC=C1CC1=CC(Br)=CC(Br)=C1O HWRPGXGZOLYUAL-UHFFFAOYSA-N 0.000 description 4
PELPQGBUZNQVLR-UHFFFAOYSA-N 2-[(4-ethylphenyl)methyl]phenol Chemical compound C1=CC(CC)=CC=C1CC1=CC=CC=C1O PELPQGBUZNQVLR-UHFFFAOYSA-N 0.000 description 4
229940127007 Compound 39 Drugs 0.000 description 4
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OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
230000001539 anorectic effect Effects 0.000 description 4
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QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 4
230000014509 gene expression Effects 0.000 description 4
230000002218 hypoglycaemic effect Effects 0.000 description 4
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 4
210000003734 kidney Anatomy 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
125000000542 sulfonic acid group Chemical group 0.000 description 4
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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RU2004135914/04A 2002-08-09 2003-08-08 ПРОИЗВОДНЫЕ АРИЛ 5-ТИО-β-D-ГЛЮКОПИРАНОЗИДА И ТЕРАПЕВТИЧЕСКИЕ СРЕДСТВА ПРИ ДИАБЕТЕ, СОДЕРЖАЩИЕ ИХ RU2322449C2 (ru)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP2002-233015		2002-08-09
JP2002233015		2002-08-09
JP2003097839		2003-04-01
JP2003-97839		2003-04-01

Publications (2)

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RU2004135914A RU2004135914A (ru)	2005-05-10
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EP (2)	EP1528066A4 (fr)
JP (2)	JPWO2004014930A1 (fr)
KR (2)	KR100588457B1 (fr)
CN (2)	CN100341885C (fr)
AU (2)	AU2003254903B9 (fr)
BR (1)	BR0310006A (fr)
CA (2)	CA2478889A1 (fr)
HK (2)	HK1077582A1 (fr)
HR (1)	HRP20040814A2 (fr)
MX (2)	MXPA04009265A (fr)
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NZ (1)	NZ535229A (fr)
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RU (1)	RU2322449C2 (fr)
TW (2)	TWI274055B (fr)
UA (1)	UA77300C2 (fr)
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ZA200407187B (en)	2006-02-22
PL372865A1 (en)	2005-08-08
JP3813160B2 (ja)	2006-08-23
CN1312165C (zh)	2007-04-25
KR100588457B1 (ko)	2006-06-12
CA2493491A1 (fr)	2004-02-19
MXPA04009265A (es)	2005-01-25
UA77300C2 (en)	2006-11-15
TW200409778A (en)	2004-06-16
BR0310006A (pt)	2005-02-15
WO2004014931A1 (fr)	2004-02-19
HK1079532A1 (en)	2006-04-07
TWI274055B (en)	2007-02-21
AU2003254903B2 (en)	2008-07-31
JPWO2004014930A1 (ja)	2005-12-02
HRP20040814A2 (en)	2005-06-30
US20050256317A1 (en)	2005-11-17
JPWO2004014931A1 (ja)	2005-12-02
AU2003254903A1 (en)	2004-02-25
MXPA05000725A (es)	2005-04-08
CN1675233A (zh)	2005-09-28
US20050209309A1 (en)	2005-09-22
NO20050650L (no)	2005-03-04
CN100341885C (zh)	2007-10-10
KR20050056194A (ko)	2005-06-14
HK1077582A1 (en)	2006-02-17
TW200406396A (en)	2004-05-01
NO20043733L (no)	2004-10-20
EP1528066A4 (fr)	2007-05-02
WO2004014930A1 (fr)	2004-02-19
KR20050018642A (ko)	2005-02-23
CN1639180A (zh)	2005-07-13
EP1541578A1 (fr)	2005-06-15
RU2004135914A (ru)	2005-05-10
AU2003254904A1 (en)	2004-02-25
US7414072B2 (en)	2008-08-19
PL375298A1 (en)	2005-11-28
US7250522B2 (en)	2007-07-31
AU2003254903B9 (en)	2008-08-21
NZ535229A (en)	2006-05-26
CA2478889A1 (fr)	2004-02-19
EP1528066A1 (fr)	2005-05-04

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US7439232B2 (en)	2008-10-21	Heteroaryl 5-thio-β-D-glucopyranoside derivatives and therapeutic agents for diabetes containing the same
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JP2006117651A (ja)	2006-05-11	Ｓｇｌｔ２の活性阻害剤
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